A pinacol rearrangement/oxidation synthetic route to hydroxyphenstatin

In an attempt to develop biologically active compounds from the inactive tr ans isomer (3a) of stilbene la, after asymmetric dihydroxylation to optical ly pure (R,R)-diol 8 the unexpected racemic diphenylacetaldehyde (9) was ge nerated via a Pinacol rearrangement. Several derivatives of diphenylacetald ehyde 9 were synthesized (11-15) and reported. Further reaction of aldehyde 9 during desilylation through autoxidative decarbonylation afforded benzop henone 2b, designated hydroxyphenstatin, a potent antitumor and antimitotic agent. Hydroxyphenstatin showed potent inhibition of the tubulin assembly (IC50 0.82 muM) and exhibited an ED50 of 2.5 mug/mL against the P388 lympho cytic leukemia cell line.